CHICAGO — In Illinois, the line between legal politics and bribery has always seemed a blurry one.

Through the years, it’s been debated in bars, argued in newspapers, litigated in court, decided by juries and appealed all the way to the Supreme Court.

Over the next two weeks, the heavyweight fight over what constitutes legal political horse trading and what is a crime will go yet another round before the 7th Circuit U.S. Court of Appeals, which is set to hear long-awaited oral arguments in two of the biggest bribery cases ever to rock Illinois politics.

On Thursday, attorneys for imprisoned former House Speaker Michael Madigan are expected to ask the appeals court for a reversal of his February 2025 conviction and 7 1/2-year sentence, arguing the prosecution flouted Supreme Court rulings reining in the use of the bribery and fraud statutes and instead stretched the laws “past their breaking points.”

Then, next week, separate legal teams representing Madigan’s former confidant, Michael McClain, and and ex-ComEd CEO Anne Pramaggiore are expected to make a similar argument to the same court in their consolidated appeal of their 2023 convictions for an alleged conspiracy to bribe Madigan.

They say the convictions stemming from the “ComEd Four” case should be “doomed” by high court decisions saying “gratuities” given to politicians without a direct connection to official action cannot be considered a bribe.

The arguments in Madigan’s case are set for 2 p.m. Thursday at the Dirksen U.S. Courthouse. Arguments in the consolidated appeal for McClain and Pramaggiore will take place Tuesday. The immediate stakes are high, as Madigan, McClain, and Pramaggiore are all currently in federal prison. But the long-term impact on Illinois politics could be even greater.

Despite the high-profile aspect of the cases being argued, there is a distinct sense of deja vu.

More than 13 years ago, attorneys for former Illinois Gov. Rod Blagojevich made strikingly similar arguments before the 7th Circuit about where the hazy line of bribery falls, where Judge Frank Easterbrook invoked President Dwight Eisenhower’s nomination of Earl Warren to the U.S. Supreme Court in exchange for the California governor’s support in the 1952 election.

That Easterbrook-led appeals panel wound up reversing several counts against Blagovjevich and sent him back to the district court for resentencing, though the judges noted he was guilty of many crimes and might not deserve any break. U.S. District Judge James Zagel in 2015 took their cue and resentenced Blagojevich to the same 14-year term he’d originally imposed.

Blagojevich’s legal saga wasn’t over from there, of course, since his friend from reality television, President Donald Trump, commuted his sentence in 2020 and later gave the former governor a full pardon, wiping out all counts of conviction.

Ironically, Blagojevich has now figured into the appeal of Pramaggiore. Not only did she officially apply for clemency from the White House, she’s paid the former governor at least $130,000 to personally lobby Trump for a pardon. Federal lobbying records show that to accept the money, Blagojevich had to disclose his legal status with Congress, noting that the president had pardoned him “for all convicted offenses.”

Madigan has also applied for clemency, but there’s no record he’s paid his old political nemesis, Blagojevich, a dime.

Madigan, 83, was sentenced in June 2025 to 7 1/2 years in prison. He reported Oct. 13 to a medium-security camp in Morgantown, West Virginia, and his current release date is in early 2032, when he would be nearly 90.

Pramaggiore, 67, entered prison in January and is due to be released in September 2027. McClain, 78, is also scheduled for release around the same time.

After a trial that stretched nearly four months, Madigan was convicted by a jury Feb. 12, 2025, on bribery conspiracy and other corruption charges. The jury found him guilty on 10 of 23 counts, including a multipronged scheme to accept and solicit payments from ComEd to Madigan associates for do-nothing subcontracts.

Madigan also was convicted on six out of seven counts — including wire fraud and Travel Act violations — regarding a plan to get Solis, who testified at length in the trial, appointed to a state board in exchange for Solis bringing Madigan business for his private law firm.

The jury acquitted Madigan of several other schemes alleged in the indictment and deadlocked on other counts, including the overarching racketeering charge.In handing down the 90-month prison term, U.S. District Judge John Robert Blakey said Madigan’s crimes represented “abuse of power at the highest level” and were aggravated by the fact that Madigan had every advantage in life, including a privileged education and a thriving law practice.

The judge also found that Madigan lied repeatedly and willfully when testifying in his own defense during the trial. Blakey called it “a nauseating display of perjury and evasion” that was “hard to watch.”

In his appeal, Madigan’s attorneys said allegations surrounding two of the central prongs in the case — the ComEd bribery scheme and Madigan’s offer to help then-Ald. Daniel Solis get a state board position — “improperly criminalizes the rough-and-tumble business of state politics in direct contradiction of recent Supreme Court rulings.”

Madigan’s lawyers also accused the U.S. attorney’s office of “throwing years’ worth of legislative action and political relationships at the jury in the hopes of making something stick.”

“To be sure, the evidence showed that ComEd and the alderman sought to curry favor with Madigan,” the appeals brief stated. “Constituents do this every day, whether through hiring politically connected individuals or offering other support to legislators. These interactions may strike federal prosecutors as unbecoming. But they do not constitute bribery.”

The filing also alleged Blakey erred in several key rulings at trial, including allowing prosecutors to proceed with a “stream of benefits” theory that did not require proof of a quid pro quo or that Madigan had agreed to be influenced “on a specific question or matter.”

In his instructions to the jury, Blakey also incorrectly defined “corruptly” under the federal bribery law known as 666, which the Supreme Court ruled in 2025 did not criminalize so-called gratuities, or benefits given to a public official after the fact, the filing alleged. Blakey also erred in instructing the jury on the Travel Act by including as predicates state offenses that do not require a quid pro quo.

Once the arguments are complete in the Madigan and McClain/Pramaggiore cases, rulings could come within a month or two.

But that’s no guarantee. In Blagojevich’s case, the 7th Circuit took more than a year and a half to rule.

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